Roxbury vacation rentals

We found 426 vacation rentals — enter your dates for availability

Discover a selection of 16 homes and other vacation rentals in Roxbury that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the amenities you need and want for your stay, such as air conditioning and WiFi. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Roxbury

Showing deals for:May 22 - May 29

Image gallery for Lakewood Farmhouse with exceptional kitchen/ great room.

Great area to cook, dine, play board games.
10 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Lakewood Farmhouse with exceptional kitchen/ great room.

Pine Hill

8% off
Price is $598
$4,186 for 7 nights
All fees included
Lakewood Farmhouse with exceptional kitchen/ great room.

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Find out more about Roxbury

Why visit Roxbury

  • Outdoor Adventures: Enjoy skiing and a variety of outdoor activities in stunning natural landscapes.
  • Cultural Experiences: Immerse yourself in the local culture and history that Roxbury uniquely offers.
  • Charming Accommodations: Choose from cozy cabins, private homes, and charming cottages for a memorable stay.
  • Family-Friendly Atmosphere: Roxbury provides a relaxing environment perfect for families and nature lovers.
  • Serene Neighborhoods: Explore nearby neighborhoods for local amenities and a tranquil vibe.

Popular types of accommodation in Roxbury

Planning a getaway to Roxbury? You've picked a fantastic destination. Discover the charm of Roxbury vacation rentals, where you'll find a variety of options including houses, cozy cabins, and charming cottages. Whether you're searching for the perfect house rental or looking for the best amenities on Vrbo, Roxbury has something to suit every traveler's needs. Dive into your next adventure with confidence and ease.

  • Houses: The top choice for visitors, these homes offer a spacious and comfortable setting for families, groups, or couples seeking privacy and convenience in Roxbury.
  • Cabins: A cozy and rustic option, cabins provide an intimate experience, perfect for those who want to immerse themselves in nature while enjoying modern comforts.
  • Cottages: These charming and quaint accommodations are ideal for travelers looking for a peaceful retreat, often featuring unique character and local flair.
  • Chalets: Offering a blend of comfort and style, chalets are particularly popular among those seeking a mountain getaway with stunning views.
  • Apartments: A convenient choice for shorter stays, apartments provide all the essential amenities in a compact space, great for couples or solo travelers.**

Top attractions in and around Roxbury

Roxbury, New York, is the perfect destination for ski and adventure enthusiasts. With attractions like national parks and ski resorts, visitors can enjoy a range of outdoor activities while soaking in the beautiful scenery. Whether you’re seeking cultural experiences or just want to explore the great outdoors, Roxbury offers something for everyone, making it an ideal spot for a memorable vacation.

  • Plattekill Mountain: A premier ski resort offering thrilling winter sports, Plattekill Mountain is perfect for both seasoned skiers and beginners. Enjoy adventure-filled outdoor activities with stunning views of the surrounding landscape, making it a year-round destination.
  • Hobart Book Village: A charming and secluded attraction, Hobart Book Village is a haven for book lovers. Explore quaint shops filled with rare and used books, all while enjoying a relaxing atmosphere that invites you to unwind and read.
  • East Branch Delaware River: This picturesque river is ideal for outdoor enthusiasts. Enjoy scenic views, fishing, and kayaking amidst tranquil surroundings, making it a perfect spot for nature lovers to connect with the great outdoors.

Things to do recommended for couples

For a romantic getaway in Roxbury, hit the slopes at Plattekill Mountain for some skiing adventure. Afterward, enjoy a wine tasting at Windham Vineyards and Winery, just 14 miles away, for a perfect blend of romance and outdoor charm. Don't miss the thrill at Belleayre Mountain Ski Center, only 12 miles away.

Things to do recommended for families

Families will love the Pine Hill Community Center, located 12 miles from Roxbury. This recreation center offers wellness activities and relaxation, making it a perfect spot for quality family time and fun-filled experiences together.

Things to do recommended for groups

Groups traveling to Roxbury can enjoy a round of golf at Stamford Golf Club or Windham Country Club for an outdoor experience. For a unique twist, visit Union Grove Distillery to savor local spirits in a romantic setting, perfect for entertainment and relaxation.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Roxbury

If you're traveling with a group, your family, or even your pets, or if you're planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

  • Traveling to Roxbury with a group: Think about how many bedrooms you require and any additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Roxbury with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Roxbury: For many families, a vacation just isn't the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Roxbury: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Roxbury

Roxbury, New York, is a hidden gem perfect for a ski or adventure getaway. Surrounded by lush greenery and historical charm, this quaint city offers a relaxing atmosphere ideal for families and nature lovers alike. Explore nearby neighborhoods for local amenities and enjoy the serene vibes that make Roxbury a perfect destination for your next vacation. Whether you're seeking thrilling sports or peaceful retreats, you’ll find an unforgettable experience in this picturesque region.

  • Grand Gorge: Grand Gorge is a charming city located 6 miles from Roxbury, making it an ideal spot for adventure seekers. Renowned for its stunning ski fields and resorts, Grand Gorge offers a plethora of outdoor activities year-round. Visitors can explore the scenic mountains, relax by tranquil lakes, or hike through beautiful parks. Whether you’re hitting the slopes in winter or enjoying the breathtaking views in summer, Grand Gorge is a perfect destination for those looking to immerse themselves in nature and exhilarating outdoor experiences.
  • Denver: Situated also 6 miles from Roxbury, Denver is a vibrant city that attracts adventure lovers and sports enthusiasts alike. Known for its proximity to ski fields and resorts, this city offers thrilling winter sports and year-round outdoor activities. With stunning mountains, picturesque lakes, and access to national state parks, Denver is an outdoor playground. Travelers can indulge in skiing, snowboarding, and hiking, or enjoy local dining and cultural experiences. Denver is a fantastic base for anyone eager to explore the great outdoors while enjoying city amenities.
  • Prattsville: Located 7 miles from Roxbury, Prattsville is a quaint city that offers a blend of adventure and outdoor recreation. Like its neighboring cities, it boasts excellent ski fields and resorts perfect for winter sports. Prattsville is surrounded by majestic mountains and serene lakes, providing ample opportunities for hiking, fishing, and enjoying nature. The local parks add to the charm, making it a great spot for families and nature lovers. Whether you’re skiing down the slopes or exploring the picturesque surroundings, Prattsville promises an unforgettable outdoor experience.

Best time to go to Roxbury

If you're planning a trip to Roxbury, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.6°F (-5.8°C)Light RainMostly CloudyAverageSlightly High
February23.4°F (-4.8°C)Light RainMostly CloudyAverageSlightly High
March30.4°F (-0.9°C)Light RainMostly CloudyAverageAverage
April41.7°F (5.4°C)Light RainMostly CloudyAverageSlightly Low
May53.8°F (12.1°C)Light RainMostly CloudyAverageSlightly Low
June61.2°F (16.2°C)Light RainMostly SunnyAverageAverage
July66.9°F (19.4°C)Light RainMostly SunnySlightly HighAverage
August64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
September58.3°F (14.6°C)Light RainMostly SunnySlightly HighSlightly Low
October47.7°F (8.7°C)Light RainMostly CloudySlightly LowAverage
November35.6°F (2.0°C)Light RainMostly CloudySlightly LowAverage
December28.0°F (-2.2°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you aiming to save on your upcoming travel plans? Being open to adjusting your travel dates can significantly impact prices, as they tend to vary. Additionally, if you opt for an extended stay, you often unlock substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire reservation. Being the planner truly has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up right where you left off, and keep your plans organized. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Roxbury getaway

Experience the unique character of Roxbury with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Roxbury

Are you looking for top things to see and do in the city? Venture out of your cozy vacation rental and experience everything that makes Roxbury a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Hunter Mountain (19 mi / 30.5 km)
  • Plattekill Mountain (4.5 mi / 7.2 km)
  • Hobart Book Village (7.4 mi / 12 km)
  • Belleayre Mountain Ski Center (11.5 mi / 18.5 km)
  • Pine Hill Community Center (12.5 mi / 20.1 km)
  • Windham Vineyards and Winery (13.7 mi / 22.1 km)

Exploring the natural landscape of Roxbury

Whether you're looking for fun outdoor activities or just want to take in the scenery, Roxbury is a great place to get out in nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • East Branch Delaware River (11.3 mi / 18.1 km)
  • Canada Falls (12.3 mi / 19.8 km)
  • Belleayre Beach (13 mi / 20.9 km)
  • Catskill Mountains (22.3 mi / 35.9 km)
  • Relay State Forest (3 mi / 4.9 km)
  • Plattekill State Forest (4.9 mi / 7.8 km)

Frequently asked questions

What is the best area to stay in Roxbury, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Roxbury, New York, the area surrounding the charming Main Street is an excellent choice. This neighborhood offers a delightful blend of small-town charm and access to some of the region's top attractions. Visitors can enjoy the scenic beauty of the nearby Catskill Mountains, superb for hiking and outdoor adventures. Additionally, the iconic Roxbury Arts Center provides a cultural touchpoint, hosting various performances and art exhibitions throughout the year.

Main Street is home to a selection of cozy properties that reflect the area's rustic aesthetic, making it a superb spot for those looking to immerse themselves in the local community.
How much does it cost to rent a vacation home in Roxbury?
Prices for vacation rentals in Roxbury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Roxbury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Roxbury vacation house rentals?
You can find great discounts on house rentals in Roxbury on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Roxbury ski resort rentals?
For the best ski resort rentals near Roxbury, New York, travelers should focus on the nearby Catskill Mountains, particularly around the town of Windham and the adjacent area of Hunter. These locations are home to popular ski resorts and offer a variety of rental options. In Windham, visitors can find cozy cabins and chalets that often come with amenities such as wood-burning fireplaces, outdoor decks with mountain views, and fully equipped kitchens, great for families or groups looking to unwind after a day on the slopes.

In Hunter, there are numerous vacation rentals, including modern condos and ski-in/ski-out lodges, which provide easy access to the ski lifts. Many of these accommodations feature amenities like hot tubs, saunas, and communal game rooms, enhancing the après-ski experience. The area is also known for its vibrant local dining scene and charming shops, making it a great place to relax and enjoy the mountain atmosphere.

Additionally, the surrounding towns offer access to various outdoor activities beyond skiing, such as snowshoeing and hiking trails, with some rentals providing equipment storage and proximity to these trails.
What is the most popular type of vacation rental accomodation in Roxbury?
In Roxbury, vacation houses are the most popular rental option, with about 13 available throughout the area. These houses often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Additionally, several cabins, cottages, and apartments can be found, each offering a cozy atmosphere with amenities like outdoor seating areas and proximity to nature trails. For travelers looking for a more rustic experience, chalets are also available, providing a unique blend of comfort and outdoor adventure.
Are there any family house rentals in Roxbury?
In Roxbury, New York, there are several family-friendly vacation rentals available, with around 16 options to choose from. This charming area is located in the Catskills, making it an excellent choice for families looking to enjoy nature and outdoor activities. Many homes in the region offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor decks or patios where families can relax and enjoy the fresh mountain air.

Visitors can also expect amenities like Wi-Fi, game rooms for entertainment, and cozy fireplaces great for chilly evenings. The locale is near the picturesque Catskill Park, providing opportunities for hiking, fishing, and exploring the beautiful landscapes. Additionally, Roxbury is close to local attractions such as the Roxbury Arts Center, which hosts various events and workshops, making it a great base for family adventures.
Can I rent a vacation home with a pool or hot tub in Roxbury?
In Roxbury, there are several vacation homes available for rent that come with pools and hot tubs, making it an appealing destination for travelers seeking relaxation and leisure. This quaint town, located in the Catskills, offers a variety of properties that may include amenities such as private swimming pools, outdoor hot tubs, and spacious backyards superb for gatherings or family fun. Many rentals also feature fully equipped kitchens and comfortable living spaces, ideal for unwinding after a day of exploring the beautiful surroundings. Find your rental in Roxbury with a pool or a hot tub.
Can I find long-stay vacation rentals in Roxbury?
A long-stay vacation rental in Roxbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Roxbury?
In Roxbury, travelers can find a selection of pet-friendly house rentals, with around eleven options available. This charming town in the Catskills is known for its picturesque landscapes and outdoor activities, making it a great choice for those traveling with pets. Many of the vacation rentals here come equipped with cozy amenities such as fireplaces, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.

The area offers access to beautiful hiking trails and scenic views, ideal for pet owners looking to explore the great outdoors. Nearby, you can find parks and natural areas that welcome pets, providing opportunities for walks and adventures in nature.
Are there any remote work vacation rentals in Roxbury?
In Roxbury, New York, there are about 18 vacation rentals that cater to remote work needs. This quaint town in the Catskills offers a peaceful environment ideal for those looking to blend work and leisure. Properties typically include amenities such as dedicated workspaces, high-speed Wi-Fi, and comfortable seating areas, ensuring a conducive atmosphere for productivity. Additionally, some rentals might feature outdoor spaces superb for taking breaks while enjoying the scenic views of the surrounding mountains. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Roxbury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Roxbury with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Roxbury?
In Roxbury, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many rentals also feature cozy decks or patios where travelers can relax and enjoy the beautiful surroundings. Fireplaces are commonly found, providing warmth and ambiance during cooler evenings. Additionally, coffee and tea makers are available for those who enjoy a warm beverage at any time of the day. Onsite parking is another amenity that travelers can expect, making it convenient for those who arrive by car.
When is the best time to visit Roxbury for a vacation rental?
The best time to visit Roxbury for a vacation rental is from July to September, with August being particularly popular among travelers seeking a vibrant summer escape. During this peak season, visitors can enjoy a wealth of outdoor activities, including hiking in the stunning Catskill Mountains and exploring the charming local shops and eateries that define the area. The warm weather, typically ranging from the mid-60s to low 80s Fahrenheit, creates an inclusive setting for both relaxation and adventure.

August, in particular, is an excellent month to immerse yourself in the local culture, as various festivals and events take place, celebrating everything from music to art. The lively ambiance during this time makes it a superb choice for families and groups looking to make lasting memories.

For those looking for more budget-friendly options, consider planning your visit in November. While this month falls outside of the bustling peak season, it offers a serene experience with fewer crowds, allowing for peaceful hikes and cozy evenings by the fire. The crisp autumn air and stunning fall colors add to the charm of the Catskills.
How early should I book a Roxbury vacation rental?
Book your Roxbury vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Roxbury, New York, United States of America?
In Roxbury, New York, visitors can explore a charming selection of attractions that highlight the area's natural beauty and rich history. The scenic Catskill Mountains provide ample opportunities for outdoor activities such as hiking and fishing, with numerous trails accessible from the town. The nearby Roxbury Arts Group offers cultural events and performances that showcase local talent, making it a focal point for arts and community engagement.

The historic district features quaint shops and eateries, where visitors can enjoy local cuisine and browse unique crafts. Additionally, the picturesque surroundings offer stunning views, especially during the fall foliage season, drawing nature enthusiasts and photographers alike.
Can I change or cancel my Roxbury home rental booking on Vrbo?
To find Roxbury vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Roxbury vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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